Hydrogen Bromide → HCID 22004117, compound

HRID 324276Notes

Reaction equation

HRID 324276 reaction equation
[ClH:1].C[O:3][C:4]1[C:12]2[N:11]=[CH:10][N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.Br>C(O)(=O)C>[ClH:1].[OH:3][C:4]1[C:12]2[N:11]=[CH:10][N:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 70247570HCID 70247570, compound

Product 1

HCID 22004117HCID 22004117, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Demethylation of 4-methoxy-1-phenylbenzimidazole hydrochloride with HBr in glacial acetic acid as described for synthesis of Example 2 gave Example 11 as the HCl salt, (77%): mp (MeOH/Et2O) 238-240° C. 1H NMR (D2O):δ9.41 (s, 1 H, H-2), 7.74-7.67 (m, 5 H, Ph), 7.47 (dd, J=8.3, 8.2 Hz, 1 H, H-6), 7.22 (d, J=8.3 Hz, 1 H, H-7), 7.08 (dd, J=8.2 Hz, 1 H, H-5); 13C NMR:δ147.45 (s), 141.70 (d), 136.00 (s), 135.85 (s), 133.32 (d), 133.10 (d), 131.01 (d), 127.47 (d), 123.81 (s), 114.17 (d), 106.90 (d).

Sources & evidence

ORD record
ord-258e433b8db04ad1a9fee41e7434f80f
Source dataset
uspto-grants-2001_04
Patent number
US06218388B1

Reaction notes

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